IBUTILIDE FUMARATE

Details

Stereochemistry	RACEMIC
Molecular Formula	2C20H36N2O3S.C4H4O4
Molecular Weight	885.225
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)\C=C\C(O)=O.CCCCCCCN(CC)CCCC(O)C1=CC=C(NS(C)(=O)=O)C=C1.CCCCCCCN(CC)CCCC(O)C2=CC=C(NS(C)(=O)=O)C=C2

InChI

InChIKey=PCIOHQNIRPWFMV-WXXKFALUSA-N

InChI=1S/2C20H36N2O3S.C4H4O4/c2*1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25;5-3(6)1-2-4(7)8/h2*12-15,20-21,23H,4-11,16-17H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;;2-1+

HIDE SMILES / InChI

Molecular Formula	C20H36N2O3S
Molecular Weight	384.576
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description

Ibutilide is a 'pure' class III antiarrhythmic drug, used intravenously against atrial flutter and fibrillation. At a cellular level it exerts two main actions: induction of a persistent Na+ current sensitive to dihydropyridine Ca2+ channel blockers and potent inhibition of the cardiac rapid delayed rectifier K+ current, by binding within potassium channel pores. In other words, Ibutilide binds to and alters the activity of hERG potassium channels, delayed inward rectifier potassium (IKr) channels and L-type (dihydropyridine sensitive) calcium channels. Ibutilide is indicated for the rapid conversion of atrial fibrillation or atrial flutter of recent onset to sinus rhythm. Ibutilide is marketed as Corvert by Pfizer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Voltage-gated L-type calcium channel alpha-1C subunit 44	Activator 1,430
Voltage-dependent L-type calcium channel subunit beta-1 2	Activator 1,430
HERG 92	Inhibitor 8,297	0.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atrial fibrillation 131	Primary		Approved 8,429	CORVERT

C_max

Value	Dose	Co-administered	Analyte	Population
5.8 μg/L	1 mg single, intravenous		IBUTILIDE unknown	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
177 μg × min/L	1 mg single, intravenous		IBUTILIDE plasma	Homo sapiens
13.2 μg × h/L	1 mg single, intravenous		IBUTILIDE unknown	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
9.1 h	1 mg single, intravenous		IBUTILIDE plasma	Homo sapiens
12.4 h	1 mg single, intravenous		IBUTILIDE unknown	Homo sapiens

Doses

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Dose	Population	Adverse events
1 mg single, intravenous Highest studied dose	healthy, adult n = 8
1 mg 1 times / 10 min multiple, intravenous Recommended	unhealthy, adult n = 776	Disc. AE: Extrasystoles ventricular, Non-sustained ventricular tachycardia... Other AEs: Chest pain, Bradycardia...

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AEs

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AE	Significance	Dose	Population
Heart arrest	1%	1 mg 1 times / 10 min multiple, intravenous Recommended	unhealthy, adult n = 776
Sinus bradycardia	1.2%	1 mg 1 times / 10 min multiple, intravenous Recommended	unhealthy, adult n = 776
Bradycardia	1.4%	1 mg 1 times / 10 min multiple, intravenous Recommended	unhealthy, adult n = 776
Diarrhea	1.8%	1 mg 1 times / 10 min multiple, intravenous Recommended	unhealthy, adult n = 776
Dizziness	1.8%	1 mg 1 times / 10 min multiple, intravenous Recommended	unhealthy, adult n = 776

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737		substrate 1,217	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1,217	substrate 3,367	no
CYP3A4 1,737	substrate 3,367	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY512832	https://www.001chemical.com/chem/122647-31-8
3B Scientific (Wuhan) Corp	3B2-1373	http://www.3bsc.com/index/pro_info.php?id=55089
AHH Chemical co.,ltd	MT-52774	http://www.ahhchemical.com/product/MT-52774.html
AK Scientific, Inc. (AKSCI)	71782	http://www.aksci.com/item_detail.php?cat=71782
AvaChem Scientific	2455B	http://www.avachem.com/productSearch.asp?2455B

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PubMed

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Title	Date	PubMed
Acute renal failure after ibutilide.	1999 Feb 6	9989724
Termination of recent-onset atrial fibrillation/flutter in the emergency department: a sequential approach with intravenous ibutilide and external electrical cardioversion.	2000 Aug 1	10959017
Drug-induced QT prolongation in women during the menstrual cycle.	2001 Mar 14	11255387
Comparison of verapamil and ibutilide for the suppression of immediate recurrences of atrial fibrillation after transthoracic cardioversion.	2002 Jul	12232564
Ibutilide-induced long QT syndrome and torsade de pointes.	2002 Nov-Dec	12424513

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Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Atrial Fibrillation 60 kg or more: 1 mg IV over 10 minutes; if arrhythmia persists 10 minutes after the end of the first infusion, repeat once. Less than 60 kg: 0.01 mg/kg IV over 10 minutes; if arrhythmia persists 10 minutes after the end of the first infusion, repeat once.

Route of Administration: Intravenous

In Vitro Use Guide

Ibutilide at the 10(-5) M effective refractory periods at 1 and 3 Hz increased by 18-32 ms, conduction times measured at 3 Hz increased by 27-30% and atrial rate decreased by 19-32% in isolated rabbit myocardium.

Substance Class	Chemical
Record UNII	9L5X4M5L6I
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

IBUTILIDE FUMARATE

Official Name

English

METHANESULFONAMIDE, N-(4-(4-(ETHYLHEPTYLAMINO)-1-HYDROXYBUTYL)PHENYL)-, (±)-, (E)-2-BUTENEDIOATE (2:1) (SALT)

Common Name

English

CORVERT

Brand Name

English

IBUTILIDE FUMARATE [MI]

Common Name

English

(±)-4'-(4-(ETHYLHEPTYLAMINO)-1-HYDROXYBUTYL)METHANESULFONANILIDE FUMARATE (2:1) (SALT)

Common Name

English

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Classification Tree

Code System

Code

Agent Affecting Cardiovascular System

NCI_THESAURUS

C47793

Pharmacologic Substance

NCI_THESAURUS

C93038

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Code System

Code

Type

Description

HSDB

7926

PRIMARY

EPA CompTox

DTXSID8048652

PRIMARY

PUBCHEM

5281065

PRIMARY

CAS

122647-32-9

PRIMARY

NCI_THESAURUS

C47561

PRIMARY

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Related Record

Type

Details


					2436VX1U9B

IBUTILIDE

PARENT -> SALT/SOLVATE

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Related Record

Type

Details


					C4FC0E82MH

N-ETHYL-N-HEPTYL-4-HYDROXY-4-(4-(METHYLSULFONAMIDO)PHENYL)BUTANAMIDE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.15] PERCENT PEAK AREA (limits)


					L3J9NB91E2

N-ETHYL-N-HEPTYL-4-(4-(METHYLSULFONAMIDO)PHENYL)-4-OXOBUTANAMIDE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.15] PERCENT PEAK AREA (limits)

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Related Record

Type

Details


					2436VX1U9B

IBUTILIDE

ACTIVE MOIETY

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2